N-bromobutanimide → HCID 57800081, compound

HRID 2101917Notes

Reaction equation

HRID 2101917 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:11]([C:12]#[N:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C1C(=O)N([Br:23])C(=O)C1>CN(C=O)C>[Br:23][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:11]([C:12]#[N:13])[C:3]=2[C:2]([F:14])([F:1])[F:15])[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 674054494-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 57800081HCID 57800081, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cold solution of 4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.047 g, 0.22 mmol) in DMF (2 mL), under N2, was added a solution of NBS (0.043 g, 0.24 mmol) in DMF (0.5 mL). The mixture was stirred in the ice bath for 30 min and then at rt for 1 h. The mixture was partitioned between Et2O and an aqueous solution of Na2S2O3. The organic phase was washed with water and sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by radial chromatography (5-50% EtOAc-hexanes gradient) to afford the title compound: 1H NMR (400 MHz, CDCl3+few drops of CD3OD) δ 11.52 (bs, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.48-7.45 (m, 2H).

Workup

  1. customThe mixture was partitioned between Et2O
  2. washThe organic phase was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by radial chromatography (5-50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-a5e19d9008114444b00901a7788083a0
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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